Flights
Meals unless stated
Travel Insurance
Day 1 – Saturday, July 25: Depart for Pittsburgh
Make your way to our host hotel the Holiday Inn Express & Suites North Shore, Pittsburgh, ideally located just a five-minute walk from PNC Park and surrounded by many of Pittsburgh’s best bars and restaurants. Make sure you plan to arrive no later than 2pm.
After settling in, we’ll head to PNC Park for a behind-the-scenes tour of this beautiful ballpark—home of the Pittsburgh Pirates—before taking our seats for tonight’s matchup: Cubs vs. Pirates.
Day 2 – Sunday, July 26: Explore the Steel City
Enjoy a leisurely breakfast (included daily), then the morning and afternoon are yours to explore Pittsburgh. Take the Monongahela Incline for panoramic views across the city’s Golden Triangle, or visit the Western Pennsylvania Sports Museum to discover the region’s rich sporting history.
Later, return to PNC Park for Game 2 of the series as the Cubs take on the Pirates once again.
Day 3 – Monday, July 27: On to Cincinnati
After breakfast, we check out and travel west to Cincinnati, where we’ll stay two nights at the Fairfield Inn & Suites. Relax and unwind before heading to Great American Ball Park to watch the Cincinnati Reds face off against the Cleveland Guardians.
Day 4 – Tuesday, July 28: Louisville Excursion
This morning, we journey south to Louisville, Kentucky, for two iconic visits. Our first stop is Churchill Downs and the Kentucky Derby Museum, where a short guided tour brings to life “the most exciting two minutes in sports.”
Next, we visit the Louisville Slugger Museum & Factory. After a boxed lunch, enjoy a tour of the legendary baseball bat factory and time to explore exhibits, take photos, and pick up souvenirs.
In the evening, we return to Cincinnati for Game 2 of the Reds–Guardians series.
Day 5 – Wednesday, July 29: The Windy City Awaits
We’re back on the road this morning, heading north to Chicago. Upon arrival, check into the Hyatt Place, then get ready for an exciting evening game at Guaranteed Rate Field, where the New York Yankees take on the Chicago White Sox.
Day 6 – Thursday, July 30: Field of Dreams & Rockford Peaches
It’s an early start for an unforgettable day trip! We travel to Dyersville, Iowa, to visit the Field of Dreams Movie Site—a must-see for every baseball fan. Enjoy a nostalgic experience playing catch on the iconic diamond, walking through the cornfield, and touring the farmhouse featured in the movie. A lunch on-site is included.
On our way back to Illinois, we’ll stop in Rockford, home of the legendary Rockford Peaches from A League of Their Own. Visit Beyer Stadium, now being lovingly restored, and explore the museum celebrating the women of the All-American Girls Professional Baseball League.
After this memorable day, we return to Chicago for a well-earned rest.
Day 7 – Friday, July 31: Wrigley Field & Yankees–Cubs Showdown
After a relaxed breakfast, enjoy a behind-the-scenes tour of historic Wrigley Field, one of baseball’s most beloved ballparks.
The afternoon is free to explore Chicago—perhaps stroll along the Magnificent Mile or enjoy a river cruise—before returning to Wrigley Field for the evening’s blockbuster game: Yankees vs. Cubs.
Day 8 – Saturday, August 1: Bound for Cleveland
Following breakfast, we depart for Cleveland and check in at Tru by Hilton Midtown for our final two nights.
In the evening, we’ll head to Progressive Field to see the Cleveland Guardians host the Arizona Diamondbacks.
Day 9 – Sunday, August 2: Rock & Baseball History
After breakfast, enjoy a behind-the-scenes tour of Progressive Field, followed by a visit to the world-famous Rock & Roll Hall of Fame, located on the Lake Erie waterfront.
The afternoon is yours to explore at your leisure before we head back to the ballpark for the Diamondbacks–Guardians Game 2—our final ballgame of the tour!
Day 10 – Monday, August 3: Homeward Bound
After one last breakfast together, we check out of the hotel and you head home, filled with great memories from this incredible baseball adventure.
We always recommend you take out Travel Insurance and below we've listed just some of the reasons why:
| Book Now | |
| All pricing is per person | |
| Single 1 guest per room | 4899 USD |
| Double 2 guests per room | 3699 USD |
| Triple 3 guests per room | 3549 USD |
| Pay deposit only | 500 USD |
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